Q.-P. Diao, H. Guo, and G.-Q. Wang
Vol 000
1-(2-(2-(4-(((4-Methyl-2-oxo-2H-chromen-7-yl)oxy)methyl)-
C25H23N5O6: C, 61.34; H, 4.74; N, 14.31; Found: C,
61.16; H, 4.48; N, 14.08.
3-(Hydroxyimino)-5-methyl-1-(2-(2-(4-(((4-methyl-2-oxo-
2H-chromen-7-yl)oxy)methyl)-1H-1,2,3-triazol-1-yl)ethoxy)
ethyl)indolin-2-one (9f). Yield: 78%. 1H NMR (400 MHz,
DMSO-d6) δ 2.28 (3H, s, –CH3), 2.41 (3H, s, –CH3), 3.44
(2H, t, –CH2–), 3.49 (2H, t, –CH2–), 3.87 (2H, t, –CH2–),
4.37 (2H, t, –CH2–), 5.22 (2H, s, –CH2O–), 6.26 (1H, s,
Ar–H), 6.80 (1H, d, Ar–H), 7.02 (1H, d, Ar–H), 7.16
(1H, s, Ar–H), 7.32–7.36 (2H, m, Ar–H), 7.73 (1H, d,
Ar–H), 8.33 (1H, s, triazole-H), 12.46 (1H, brs, NOH).
ESI-MS m/z: 504 [M+H]+. Elemental Anal. Calcd (%)
for C26H25N5O6: C, 62.02; H, 5.00; N, 13.91; Found: C,
61.87; H, 4.82; N, 13.76.
1H-1,2,3-triazol-1-yl)ethoxy)ethyl)indoline-2,3-dione (9a).
1
Yield: 39%. H NMR (400 MHz, DMSO-d6) δ 2.38 (3H,
s, –CH3), 3.42 (2H, t, –CH2–), 3.46 (2H, t, –CH2–),
3.86 (2H, t, –CH2–), 4.38 (2H, t, –CH2–), 5.20 (2H, s,
–CH2O–), 6.24 (1H, s, Ar–H), 6.86 (1H, d, Ar–H), 6.98
(1H, d, Ar–H), 7.04–7.08 (2H, m, Ar–H), 7.50–7.53 (2H,
m, Ar–H), 7.68 (1H, d, Ar–H), 8.32 (1H, s, triazole-H).
ESI-MS m/z: 475 [M+H]+. Elemental Anal. Calcd (%)
for C25H22N4O6: C, 63.29; H, 4.67; N, 11.81; Found: C,
63.05; H, 4.39; N, 11.63.
5-Methyl-1-(2-(2-(4-(((4-methyl-2-oxo-2H-chromen-7-yl)
oxy)methyl)-1H-1,2,3-triazol-1-yl)ethoxy)ethyl)indoline-2,3-
dione (9b). Yield: 42%. 1H NMR (400 MHz, DMSO-d6)
δ 2.28 (3H, s, –CH3), 2.40 (3H, s, –CH3), 3.44 (2H, t,
–CH2–), 3.48 (2H, t, –CH2–), 3.86 (2H, t, –CH2–), 4.39
(2H, t, –CH2–), 5.25 (2H, s, –CH2O–), 6.25 (1H, s, Ar–
H), 6.80 (1H, d, Ar–H), 7.04 (1H, d, Ar–H), 7.15 (1H, s,
Ar–H), 7.35–7.39 (2H, m, Ar–H), 7.75 (1H, d, Ar–H),
8.36 (1H, s, triazole-H). ESI-MS m/z: 489 [M+H]+.
Elemental Anal. Calcd (%) for C26H24N4O6: C, 63.93; H,
4.95; N, 11.47; Found: C, 63.76; H, 4.82; N, 11.24.
5-Chloro-3-(hydroxyimino)-1-(2-(2-(4-(((4-methyl-2-oxo-2H-
chromen-7-yl)oxy)methyl)-1H-1,2,3-triazol-1-yl)ethoxy)ethyl)
indolin-2-one (9g).
Yield: 83%. 1H NMR (400 MHz,
DMSO-d6) δ 2.41 (3H, s, –CH3), 3.42 (2H, t, –CH2–),
3.48 (2H, t, –CH2–), 3.86 (2H, t, –CH2–), 4.38 (2H, t,
–CH2–), 5.21 (2H, s, –CH2O–), 6.26 (1H, s, Ar–H), 6.82
(1H, d, Ar–H), 6.98 (1H, d, Ar–H), 7.08 (1H, s, Ar–H),
7.30 (1H, d, Ar–H), 7.67 (1H, d, Ar–H), 7.82 (1H, s, Ar–
H), 8.32 (1H, s, triazole-H), 12.28 (1H, brs, NOH). ESI-
MS m/z: 524 [M+H]+, 526 [M+2+H]+. Elemental Anal.
Calcd (%) for C25H22ClN5O6: C, 57.31; H, 4.23; N,
13.37; Found: C, 57.06; H, 4.01; N, 13.15.
5-Chloro-1-(2-(2-(4-(((4-methyl-2-oxo-2H-chromen-7-yl)
oxy)methyl)-1H-1,2,3-triazol-1-yl)ethoxy)ethyl)indoline-2,3-
dione (9c). Yield: 46%. 1H NMR (400 MHz, DMSO-d6)
δ 2.41 (3H, s, –CH3), 3.43 (2H, t, –CH2–), 3.48 (2H, t,
–CH2–), 3.88 (2H, t, –CH2–), 4.38 (2H, t, –CH2–), 5.22
(2H, s, –CH2O–), 6.27 (1H, s, Ar–H), 6.82 (1H, d, Ar–
H), 6.99 (1H, d, Ar–H), 7.10 (1H, s, Ar–H), 7.33 (1H, d,
Ar–H), 7.68 (1H, d, Ar–H), 7.84 (1H, s, Ar–H), 8.30
(1H, s, triazole-H). ESI-MS m/z: 509 [M+H]+, 511 [M
+2+H]+. Elemental Anal. Calcd (%) for C25H21ClN4O6:
C, 59.00; H, 4.16; N, 11.01; Found: C, 58.74; H, 3.88;
N, 10.86.
5-Fluoro-3-(hydroxyimino)-1-(2-(2-(4-(((4-methyl-2-oxo-2H-
chromen-7-yl)oxy)methyl)-1H-1,2,3-triazol-1-yl)ethoxy)ethyl)
indolin-2-one (9h).
Yield: 54%. 1H NMR (400 MHz,
DMSO-d6) δ 2.42 (3H, s, –CH3), 3.42 (2H, t, –CH2–),
3.48 (2H, t, –CH2–), 3.88 (2H, t, –CH2–), 4.39 (2H, t,
–CH2–), 5.22 (2H, s, –CH2O–), 6.26 (1H, s, Ar–H), 6.89
(1H, d, Ar–H), 7.04 (1H, d, Ar–H), 7.09 (1H, s, Ar–H),
7.18 (1H, d, Ar–H), 7.65 (1H, d, Ar–H), 7.73 (1H, s, Ar–
H), 8.34 (1H, s, triazole-H), 12.38 (1H, brs, NOH). ESI-
MS m/z: 508 [M+H]+. Elemental Anal. Calcd (%) for
C25H22FN5O6: C, 59.17; H, 4.37; N, 13.80; Found: C,
58.89; H, 4.14; N, 13.63.
5-Fluoro-1-(2-(2-(4-(((4-methyl-2-oxo-2H-chromen-7-yl)
oxy)methyl)-1H-1,2,3-triazol-1-yl)ethoxy)ethyl)indoline-2,3-
dione (9d). Yield: 33%. 1H NMR (400 MHz, DMSO-d6)
δ 2.42 (3H, s, –CH3), 3.44 (2H, t, –CH2–), 3.48 (2H, t,
–CH2–), 3.87 (2H, t, –CH2–), 4.39 (2H, t, –CH2–), 5.21
(2H, s, –CH2O–), 6.26 (1H, s, Ar–H), 6.88 (1H, d, Ar–
H), 7.01 (1H, d, Ar–H), 7.07 (1H, s, Ar–H), 7.16 (1H, d,
Ar–H), 7.66 (1H, d, Ar–H), 7.72 (1H, s, Ar–H), 8.33
(1H, s, triazole-H). ESI-MS m/z: 493 [M+H]+. Elemental
Anal. Calcd (%) for C25H21FN4O6: C, 60.97; H, 4.30; N,
11.38; Found: C, 60.76; H, 4.12; N, 11.19.
3-(Methoxyimino)-1-(2-(2-(4-(((4-methyl-2-oxo-2H-
chromen-7-yl)oxy)methyl)-1H-1,2,3-triazol-1-yl)ethoxy)ethyl)
indolin-2-one (9i).
Yield: 69%. 1H NMR (400 MHz,
DMSO-d6) δ 2.46 (3H, s, –CH3), 3.42 (2H, t, –CH2–),
3.47 (2H, t, –CH2–), 3.84 (2H, t, –CH2–), 4.24 (3H, s,
NOCH3), 4.36 (2H, t, –CH2–), 5.24 (2H, s, –CH2O–),
6.27 (1H, s, Ar–H), 6.92 (1H, d, Ar–H), 7.04 (1H, d, Ar–
H), 7.09–7.13 (2H, m, Ar–H), 7.35 (1H, t, Ar–H), 7.72
(1H, d, Ar–H), 7.84 (1H, d, Ar–H), 8.36 (1H, s, triazole-
H). ESI-MS m/z: 504 [M+H]+. Elemental Anal. Calcd
(%) for C26H25N5O6: C, 62.02; H, 5.00; N, 13.91;
Found: C, 61.76; H, 4.74; N, 13.68.
3-(Methoxyimino)-5-methyl-1-(2-(2-(4-(((4-methyl-2-oxo-
2H-chromen-7-yl)oxy)methyl)-1H-1,2,3-triazol-1-yl)ethoxy)
ethyl)indolin-2-one (9j). Yield: 73%. 1H NMR (400 MHz,
DMSO-d6) δ 2.25 (3H, s, –CH3), 2.40 (3H, s, –CH3), 3.42
(2H, t, –CH2–), 3.47 (2H, t, –CH2–), 3.87 (2H, t, –CH2–),
3-(Hydroxyimino)-1-(2-(2-(4-(((4-methyl-2-oxo-2H-
chromen-7-yl)oxy)methyl)-1H-1,2,3-triazol-1-yl)ethoxy)ethyl)
indolin-2-one (9e).
Yield: 56%. 1H NMR (400 MHz,
DMSO-d6) δ 2.40 (3H, s, –CH3), 3.42 (2H, t, –CH2–),
3.48 (2H, t, –CH2–), 3.86 (2H, t, –CH2–), 4.36 (2H, t,
–CH2–), 5.21 (2H, s, –CH2O–), 6.25 (1H, s, Ar–H), 6.84
(1H, d, Ar–H), 6.99 (1H, d, Ar–H), 7.06–7.12 (2H, m,
Ar–H), 7.54–7.62 (2H, m, Ar–H), 7.71 (1H, d, Ar–H),
8.33 (1H, s, triazole-H), 12.34 (1H, brs, NOH). ESI-MS
m/z: 490 [M+H]+. Elemental Anal. Calcd (%) for
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet